Hey, I’m Pablo - an entrepreneur & VC investor turned executive coach. I partner with mission-driven leaders to help amplify their impact by unlocking real healing, growth, and change.
My Approach
We can use the challenges that leadership presents to complete the process of growing up and becoming the actualized adult we were born to be.
You will find that many seemingly business-y/tactical struggles (e.g., communicating effectively at a board meeting, navigating an executive who we find to be difficult, conveying a difficult message to our team at an All-Hands, or managing strong anxiety as a manager or key contributor often have deeper psychoemotional roots. In coaching, we see these openings as opportunities to dive deeper. We use them to uncover conditioned habit patterns, limiting beliefs, and old self-identities. Deeper awareness brings actualization and a natural unburdening. Clients often describe a big sense of relief during sessions, which comes with a greater sense of ease, effectiveness, joy, possibility, and connection as a leader and human being.
These openings also directly impact our performance as leaders, and we work on that level as well. Throughout our engagement we cycle between both outer and inner work. Your outer work helps you drive impact (goals, priorities, plans of action, strategies). Your inner work helps you create alignment (self awareness, values, emotional conditioning, somatics). Cycling between the two unlocks an upward spiral of growth & change.
How it works
I don’t subscribe to a “templatized” version of coaching with a pre-set curriculum or required exercises. My goal is to meet you where you’re at. Together, we build a customized container where the work happens.
Here’s a sketch of what 1-on-1 coaching looks like in practice:
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We kick things off with a 60-minute "discovery session" where I ask a lot of questions. I am eager to understand your core needs and values. We explore what you would like to get out of coaching and what you need to make it a powerful experience. We then hit on some of the core agreements so that you leave feeling excited about coaching and ready to fully step in.
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The core container of the relationship is a 60 minute coaching session that happens either weekly or every other week. Our conversations center around whatever topic is “up” for you — something you’re grappling with that has you feeling stuck, energized, confused, joyful, angry, etc. I’ll ask questions to help us find our way towards understanding what is important to you, how it’s related to your goals, and ways you can take action. Sometimes it’ll feel like an “outer work” strategy session, other times like an “inner work” parts work session. I wrap up a session with takeaways, next steps, and accountability.
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Some of our coaching sessions will be more structured. When we come across topics that I have expertise guiding — e.g. clarify your values, hone your communication style, explore different “parts” of your identity, execute a round of layoffs compassionately, develop a fundraising storyline, etc. — I’ll proactively offer this more structured approach.
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I’m also available between sessions if you need more help. You can text or email any time. We can also book an additional “spot” coaching session if you find yourself in a time-sensitive situation where coaching could be useful. (This is included in my monthly coaching retainer and does not cost extra.)
This coaching format offers a steady heartbeat of support — so you make consistent progress towards your goals — while staying flexible and responsive to whatever is most alive for you.
Plans
I offer a variety of plans for leaders at different stages of development. If you’re curious about the possibility of working together, feel free to book a call and let's get to know each other :)
1-1 coaching
Two to three 60-minute 1-on-1 calls per month, with additional support as needed. Customized developmental container including practices, self-reflection & self-observation exericses.
Co-Founder coaching
Same as 1-on-1 coaching plus a three-way call at least every other month. Perfect for co-founders or exec team colleagues.
Group coaching
Two 90-minute group coaching calls per month with ~6 other like-minded leaders. Great for early-stage founders or leaders.
For every option, I work on a monthly retainer rather than a per-session fee. This monthly retainer covers all of our coaching sessions, plus the time I’ll spend on prep, follow-ups and any between-session support you need.
Frequently Asked Questions
I work on a monthly retainer rather than a per-session fee. This monthly retainer covers our coaching sessions, plus any additional advisory support, document review, and/or ad-hoc "sparring sessions" you might need.
My standard monthly retainer for 1-on-1 coaching is $1150 USD per month. For students, early stage founders, folks in transition, and/or those in need I hold a select number of slots under a subsidized rate, where one can choose the amount that's right for them within the range of $650-1150 USD. I do my best to never turn anyone away for lack of funds. Please reach out at plagosallegre@gmail.com if interested in exploring further.
An average executive coaching engagement lasts around nine months, but mileage varies. I ask for an initial 3 month time + energy commitment because I find it’s helpful to set a time frame for us to work together without having to re-evaluate after each session. Thereafter, I like to keep it open-ended and check in every ~3 months (or after key milestones) so we can mutually decide how long to keep working together.
This depends on your goals, but my clients typically start to feel the impact of coaching within the first two months. I’ve had some clients who experience an “aha” moment in the first session or two.
In our initial “discovery” coaching session I work with you to get a clear sense for what success looks like for you and we use this to guide our coaching time together.
I sometimes text or email to follow up on something we’ve discussed but you can lean on me as needed. You can text or email me with questions that are either pressing or might benefit from more reflection, documents you want me to review (e.g., fundraising materials, development plans, outlines for difficult conversations, etc.), or even an intro or contact. If you're not sure, just ask.
My ideal clients care deeply, are profoundly curious, want to lead by example, and are committed to the process. They’re intrinsically driven to live a true expression of themselves, and are willing to take on whatever challenges that stand in the way. Historically, my clients include startup founders and key contributors; big tech VPs, directors, and senior managers; PE & VC investors; and folks in the midst of a career transition or in the search of their next calling!
About
Leadership development lights me up. Having the opportunity to support others on their own journeys is a dream come true.
I am a former VC investor and venture-backed founder turned executive coach with a deep calling for leadership & spiritual development. I spent the last 15+ years racking up professional experiences while living and working in LatAm, Asia-Pacific, East Africa, and the US as a management consultant, an operator in "corporate" e-commerce and marketplaces, in social enterprise, and most recently in tech both as a founder and investor. Over time I have learned to turn inward to unlock the most profund kind of self-development. "Wherever you go, there you are." - Jon Kabat-Zinn.
As a venture-backed Founder & CEO at Neta, a B2B platform backed by investors like Founders Fund and Kaszek, I lived through some of the most emotionally challenging periods of my life. When the market turned and the cash dried up... while building in an extremely capital intensive category. The loneliness, the anxiety, the despair. Something my business school education hadn't prepared me for. A true time of reckoning that shook me to my core. That experience rekindled my spiritual inclination and my interest in coaching.
Since then, I've completed several coach trainings, including three 6+ month intensives under the Co-Active Training Institute, Upbuild, and Aletheia. I have also been mentored myself by some of the greats, including Jeff Weiner (Chairman & ex-CEO LinkedIn) and Dan Putt (cofounder @ Reboot). And I have spent a cumulative of 6+ months in silent meditation at Buddhist Centers; my spiritual & mindfulness-based practice is a strong influence in my coaching. Coaching has become my life's work.
I hold an MBA from Stanford and can track my passion for leadership development and my beginnings as a coach to my time there. While at Stanford, I was selected by faculty to serve as an Arbuckle Leadership Fellow and got to coach my first 9 clients :)
